Aromatic amines can be alkylated selectively in an ortho position by reaction with an olefin in the presence of an aluminum anilide catalyst. Such reactions are described in Kolka et al, U.S. Pat. No. 2,814,646; Stroh et al, U.S. Pat. No. 3,275,690; Klopfer, U.S. Pat. No. 3,923,892 and Governale et al, U.S. Pat. No. 4,128,582. It is also known that tert-alkyl groups on phenols can be redistributed using sulfuric acid catalysts, cf U.S. Pat. No. 3,418,380. Similarly, methyl groups on phenols have been redistributed using an alumina catalyst, cf U.S. Pat. No. 3,417,149. Transalkylation of phenol by sec-alkyl and tert-alkyl phenols using an aluminum phenoxide catalyst is described in U.S. Pat. No. 3,933,927.
The prior art has not shown, however, how to methylate anilines in the ortho or other ring positions since no olefin can provide a methyl group.